Credit where it's due: this is based on an original idea and draft by Penton, but I revised and remade it so thoroughly that he said I might as well post it myself.

Notice the confusion about whether Dr Wondertainment is male, or female, or an organization. That's deliberate; in fact, Headless isn't capable of understanding that it's even a question. Consider the phenomenon of tautomerism, and how it might apply to identity.

The thing about years: Headless (as do most, if not all, of the other Little Misters) lives through years several times each, and not necessarily in order. He has no idea that there's anything unusual about this; doesn't everyone do it? How else can you be in more than one place at a time, and do more than one thing at a time? Although lately, it seems to have stopped happening… and if you were to ask the other Little Misters, they'd agree that the last few years have all been consecutive, and only once each, and isn't that strange?

Note that odd naivete about the world. It's not just that he doesn't know the word 'gun', he's missing other details too. But what can you expect of someone who spends >99% of his life in attics and closets and storage compartments?

At first I was wondering why that one side affect of SCP-2287 was needed (the feeling of disconnection and slower movement), since it didn't seem to play into much in the interview log. Then I realized why the car crashes were happening.

I've been really dead-set against filling out the Misters, but I have to say, between his personality and the "other people see themselves as headless" effect, this is pretty neat. His backstory makes sense, his confusion about the world is interesting. This adds to the Little Mister canon overall, ergo, I welcome it. :) +1

At first I wasn't very impressed, but then I figured 2287 was headless in less conventional ways than the physical one - in fact, he's not quite real himself. He's got a physical form and he speaks, but the fact that people see him as headless versions of themselves, and the fact that he is able to wear headpieces despite the lack of presence of a head, and the fact that he does not experience a sense of self like normal people - primes me to suggest that there's not much to him left besides perhaps a bundle of taped responses imprinted on some kind of sensory-fuckery magic like a hologram. Voct (in a chat PM) wanted to point out how Mr. Headless can't just say his name - he has to say "Mister Headless, spooky Halloween fun for the whole family!" So until someone more astute comes along and makes a better post, my final impression is that this poor guy isn't much of a guy any more, and there's not much of him to sympathise with - as much as one can sympathise with an empty shell. +1 for the implications.